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After the release of their debut album Tigermilk, Belle and Sebastian were approached by a number of record labels. They signed with the independent label Jeepster Records in the interests of staying independent creatively. Jeepster was willing to accept some of the group's other demands, such as releasing no singles, not doing press or promotional events, and not appearing in promotional materials.[2]

The band began releasing the new material, written by Murdoch, after signing with Jeepster. The album took five days to record and three to mix, slightly longer than Tigermilk. It was recorded in the same studio as Tigermilk and engineer Tony Doogan worked with the band's previous engineer to maintain a similar recording's style. Band member Sarah Martin likened Tigermilk and If You're Feeling Sinister to Rubber Soul and Revolver in the sense that the two albums were recorded quickly after one another.[3]

If You're Feeling Sinister received critical acclaim. Pitchfork placed it at number 14 in its top 100 albums of the 1990s.[16] Later, the readers of Pitchfork voted the album the 31st greatest album since the website launched in 1996.[17]Rolling Stone featured the album at number 75 on its list of "100 Best Albums of the Nineties,"[18] while Spin included the record at number 59 on its "125 Best Albums of the Past 25 Years" list.[19]If You're Feeling Sinister also appears as an entry in the book 1001 Albums You Must Hear Before You Die as chosen by music critics.[20]

In 2007, as part of the 33⅓ series, Scott Plagenhoef wrote a book about the album.

In February 2013, Pitchfork.tv released an hour-long documentary about the album directed by RJ Bentler. For the documentary every band member who played on the album was interviewed. It featured archive photographs and videos from the band's early days.[21]

If You're Feeling Sinister had sold nearly 200,000 copies by the end of 2006.[22]